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Organic Chemistry - Aromaticity, Huckle Rules, Aromatic Heterocyclic
Organic Chemistry - Aromaticity, Huckle Rules, Aromatic Heterocyclic
Organic Chemistry - Aromaticity, Huckle Rules, Aromatic Heterocyclic
COM P O U N DS ( 1 )
Aromaticity
The H u c kl e’s R u l e
e te ro c yc l es
Aromatic H
Aromaticity…
other
Benzene is unusually stable, it is 150 kJ/mol (36 kcal/mol) more stable than might be
benzene-like expected
aromatic
Benzene undergoes substitution reactions that retain the cyclic conjugation rather than electrophilic
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Benzene is a resonance hybrid whose structure is intermediate between two line-bond
characteristics structure
The Hückle’s Rule…
A molecule is aromatic
only if it has a planar,
monocyclic system of
conjugation and contains
a total of 4n + 2 p
electrons
- Erich Hückel (1931)-
The Hückle’s Rule…
The
Hücke Only molecules with 2, 6, 10, 14, 18,… p electrons can be
aromatic
l’s rule Molecules with 4n p electrons (4, 8, 12, 16,…) can not be aromatic, said to be antiaromatic
because delocalization of their p electrons would lead to their destablization
The Hückle’s Rule…
the Hückel’s
rule is Benzene It’s Aromatic
The Hückle’s Rule…
• Benzene’s Orbital Energy
p6* _____
p1 _____
The Hückle’s Rule…
Contains four p electrons wich are localized into two double bonds
Examples of rather than delocalized around the ring
the Hückel’s
rule is Antiaromatic, highly reactive, shows none of the properties
Cyclobutadien associated with aromaticity
e
The Hückle’s Rule…
• Cyclobutadiena’s Orbital Energy
p4* _____
E p2 _____ _____ p3
p1 _____
The Hückle’s Rule…
Contains eight p electrons which are localized onto four double bonds rather than delocalized around the ring
Examples of
the Hückel’s
Not aromatic
rule is
Cyclooctatetra The molecule is tub-shaped rather than planar
ene
The Hückle’s Rule…
• Cyclooctatetraene’s Orbital Energy
p8* _____
p1 _____
Aromatic, Antiaromatic, Not Aromatic
• Hydrocarbons with the cycle conjugated
structures calls Annulenes
Cyclopentadiene is not
an Aromatic compound
nor Antiaromatic
Aromatic, Antiaromatic, Not Aromatic
• How about Cyclopentadiene and it’s ion
Aromatic, Antiaromatic, Not Aromatic
• How about Cyclopentadiene and it’s ion
Antiaromatic Aromatic
Aromatic Heterocycle
The nitrogen atom is also sp2-hybridized and has one electron in a p orbital, bringing the
total to six p electrons
Pyridin The nitrogen lone pair electrons are in an sp2 orbital in the plane of the ring and are not
e
involved with the aromatic p system
Aromatic Heterocycle
Pyrimi Both nitrogens are sp2-hybridized, and each contributes one electron to the aromatic p
dine
system
Aromatic Heterocycle
The sp2-hybridized nitrogen atom contributes the two electrons from its lone pair, which occupies a p orbital
Aromatic Heterocycle
Thioph The sulfur atom is sp2-hybridized and has a lone pair of electrons in a p orbital perpendicular to the plane of the ring
ene Sulfur also has a second lone pair of electrons in the ring plane
Conclution…
The Criteria of Aromaticity…
Cyclic Planar
Conjugate satisfy
d Huckel’s rule
Your Tasks Now…
The Answers is…
1. a. b. c.
2. - Cyclic
- Conjugated
- Satisfied the Hückle’s rule
- π electrons = 12
- Aromatic / Anti-aromatic / Not aromatic
The Answers is…
3. - Cyclic
- Conjugated
- Satisfied the Hückle’s rule
O - π electrons = 6
- Aromatic / Anti-aromatic / Not aromatic
The Answers is…
4. - Cyclic
N - Conjugated
- Satisfied the Hückle’s rule
- π electrons = 6
- Aromatic / Anti-aromatic / Not aromatic
The Answers is…
5. - Cyclic
- Conjugated